Dithieno[3,2-b:2',3'-d]pyrrole-based oligothiophenes: Structural effects on fluorescence efficiency and models of effective conjugation length

ORGN 590

Brett T. Erpelding, brett.erpelding.1@ndsu.edu, Hong Mo, hong.mo@ndsu.edu, Adam R. Wohl, adam.wohl@ndsu.edu, and Seth C. Rasmussen, seth.rasmussen@ndsu.edu. Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, ND 58105
Over the last couple of decades there has been considerable fundamental and technological interest in the development of conjugated organic materials, particularly oligo- and polythiophenes. A recent approach to the design of improved oligothiophenes is the combination of the stability of the thiophene ring with the planarity of linear acenes such as pentacene. Our group has previously shown that incorporation of the fused-ring dithieno[3,2-b:2¢,3¢-d]pyrrole (DTP) unit into oligothiophenes results in oligomers that exhibit enhanced fluorescence. In efforts to better understand oligomer structural effects on the fluorescent properties of various mixed DTP-based oligomers, the parent oligomers 2,2'-bis(dithieno[3,2-b:2',3'-d]pyrrole) and quaterthiophene have been synthesized as valuable reference materials. Investigation of the fluorescent characteristics of the parent structures and mixed oligomers should give insight into the degree to which fluorescence is modulated by varying structures containing both DTP and thiophene units. Synthesis and spectroscopic characterization of the parent and mixed oligomers will be presented.
 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008